US5342868A - Crystalline synthetic resin composition - Google Patents
Crystalline synthetic resin composition Download PDFInfo
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- US5342868A US5342868A US08/026,479 US2647993A US5342868A US 5342868 A US5342868 A US 5342868A US 2647993 A US2647993 A US 2647993A US 5342868 A US5342868 A US 5342868A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
Definitions
- the present invention relates to a crystalline synthetic resin composition, in particular, a crystalline synthetic resin composition comprising a synthetic resin compounded with an alkali metal compound and a basic polyvalent metal salt of a cyclic organophosphoric ester and having improved transparency, mechanical properties, etc.
- Crystalline synthetic resins such as polyethylene, polypropylene, polybutene-1, polyethylene terephthalate, polybutylene terephthalate, polyphenylene sulfide and polyamide suffer from the fact that their mold cycling efficiency is low due to a low crystallization rate after heat melt molding and that they shrink due to the crystallization which proceeds after the heat molding.
- Other defects of these crystalline synthetic resins include an insufficient strength and a poor transparency due to the formation of large crystals.
- nucleating agent or a crystallization accelerator in order to overcome these defects, and those used heretofore include metal salts of carboxylic acids, such as aluminum 4-tert-butylbenzoate and sodium adipate; metal salts of acidic phosphoric esters, such as sodium bis(4-tert-butylphenyl) phosphate and sodium 2,2'-methylenebis(4,6-di-tert-butylphenyl) phosphate; and polyhydric alcohol derivatives such as dibenzylidenesorbitol and bis(4-methylbenzylidene)-sorbitol.
- carboxylic acids such as aluminum 4-tert-butylbenzoate and sodium adipate
- acidic phosphoric esters such as sodium bis(4-tert-butylphenyl) phosphate and sodium 2,2'-methylenebis(4,6-di-tert-butylphenyl) phosphate
- polyhydric alcohol derivatives such as dibenzylidenesorb
- metal salts of cyclic phosphoric esters of alkylidenebisphenols described in, for example, Japanese Patent Laid-Open Nos. 1736/1983 and 184252/1984 have remarkable effects and, therefore, they are widely used.
- Japanese Patent Laid-Open No. 69853/1988 discloses a method of preventing the rigidity from being reduced when an alkali metal aromatic phosphate nucleating agent is used in combination with an alkaline earth metal carboxylate such as calcium stearate by using hydrotalcite or an alkali metal carboxylate in place of the alkaline earth metal carboxylate; Japanese Patent Laid-Open Nos.
- 129050/1989 and 129051/1989 disclose a method wherein a combination of a metal salt of a cyclic organophosphoric ester with a salt of an aliphatic carboxylic acid with a group II metal of the periodic table is used;
- Japanese Patent Laid-Open Nos. 79649/ 1991 and 81368/1991 disclose a method wherein a combination of an acidic organophosphoric ester compound with a metal salt of an aliphatic carboxylic acid is used; and Japanese Patent Laid-Open No.
- 43437/1991 discloses a method of preventing the pH from lowering by immersion of a metal salt of a cyclic organophosphoric ester in hot water after irradiation with a radiation by combining it with a hydroxide of an alkali metal, alkaline earth metal or aluminum-group metal.
- Japanese Patent Laid-Open Nos. 104638/ 1989, 104639/1989 and 104647/1989 disclose the use of a basic aluminum salt of an aromatic phosphoric diester in order to improve the processability and thermal rigidity of a high-rigidity propylene resin, scarcely any effect of improving the transparency is obtained by using such a compound. It has been supposed that such a basic polyvalent metal salt compound has only a poor effect of improving the transparency of the crystalline synthetic resins.
- the inventors After intensive investigations made under these circumstances, the inventors have found that the transparency of the crystalline synthetic resins can be remarkably improved and, in addition, mechanical strengths thereof can also be improved by adding an alkali metal carboxylate, alkali metal ⁇ -diketonate or alkali metal salt of ⁇ -ketoacetic ester or basic polyvalent metal salt of cyclic organophosphoric ester to the resin.
- the present invention has been completed on the basis of this finding.
- the present invention provides a crystaline synthetic resin composition
- a crystaline synthetic resin composition comprising 100 parts by weight of a crystalline synthetic resin compounded with (a) 0.01 to 5 parts by weight of at least one of alkali metal carboxylates, alkali metal ⁇ -diketonates and alkali metal salts of ⁇ -ketoacetic esters and (b) 0.01 to 5 parts by weight of at least one of basic polyvalent metal salts of cyclic organophosphoric esters of the following general formula (I): ##STR2## wherein R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 2 and R 3 each represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, M represents a group III or IV metal atom of the periodic table, and X represents HO--when M represents a group III metal atom of the periodic table and X represents 0 ⁇ or (HO) 2 - when M represents a group IV metal atom of the periodic
- the crystalline synthetic resin composition of the present invention is improved in transparency and also in other properties such as mechanical strengths.
- alkali metals constituting the alkali metal salt compounds (a) such as alkali metal carboxylates, alkali metal ⁇ -diketonates and alkali metal salts of ⁇ -ketoacetic esters include lithium, sodium and potassium.
- the carboxylic acids constituting the alkali metal carboxylates include aliphatic monocarboxylic acids such as acetic, propionic, acrylic, octylic, isooctylic, nonanoic, decanoic, lauric, myristic, palmitic, stearic, oleic, ricinoleic, 12-hydroxystearic, behenic, montanic, melissic, ⁇ -dodecylmercaptoacetic, ⁇ -dodecylmercaptopropionic, ⁇ -N-laurylaminopropionic and ⁇ -N-methyl-N-lauroylaminopropionic acids; aliphatic polycarboxylic acids such as malonic, succinic, adipic, maleic, azelaic, sebacic, dodecanedioic, citric, butanetricarboxylic and butanetetracarboxylic acids; allcyclic mono- and
- the ⁇ -diketone compounds constituting the abovedescribed alkali metal ⁇ -diketonates include acetylacetone, pivaloylacetone, palmitoylacetone, benzoylacetone, pivaloylbenzoylacetone and dibenzoylmethane.
- the ⁇ -diketoacetic esters constituting the above-described alkali metal salts of ⁇ -ketoacetic esters include ethyl acetoacetate, octyl acetoacetate, lauryl acetoacetate, stearyl acetoacetate, ethyl benzoylacetate and lauryl benzoylacetate.
- alkali metal carboxylates, alkali metal ⁇ -diketonates and alkali metal salts of ⁇ -ketoacetic esters used as the component (a) are salts of the above-described alkali metals with carboxylic acids, ⁇ -diketone compounds and ⁇ -ketoacetic esters, respectively. They can be produced by any method known in the art.
- alkali metal salt compounds (a) preferred are alkali metal salts of aliphatic monocarboxylic acids, still preferably lithium salts of aliphatic carboxylic acids, particularly aliphatic monocarboxylic acids each having 8 to 20 carbon atoms.
- the amount of the alkali metal carboxylate, alkali metal ⁇ -diketonate or alkali metal salt of ⁇ -ketoacetic ester to be used as the component (a) is 0.01 to 5 parts by weight, particularly preferably 0.05 to 3 parts by weight, for 100 parts by weight of the crystalline synthetic resin.
- the alkyl group R 1 having 1 to 4 carbon atoms includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl and isobutyl
- the alkyl groups R 2 and R 3 having 1 to 12 carbon atoms includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, amyl, tert-amyl, hexyl, heptyl, octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl and tert-dode
- the group III and IV metal atoms, M, of the periodic table include aluminum, gallium, germanium, tin, titanium and zirconium, among which aluminum is particularly preferred.
- examples of the basic polyvalent metal salts of cyclic organophosphoric esters of the general formula (I) include the following compounds (compound ##STR3##
- the basic polyvalent metal salts of cyclic organophosphoric esters can be easily produced by, for example, a process which comprises reacting an alkali metal salt of an acidic cyclic organophosphoric ester with a polyvalent metal halide or oxidized polyvalent metal halide and, if necessary, hydrolyzing the reaction product, or a process which comprises reacting an acidic cyclic organophosphoric ester with a polyvalent metal alkoxide and, if necessary, hydrolyzing the reaction product.
- zirconium content 8.56% (calculated: 8.47%)
- the particle diameter of the basic polyvalent metal salts of cyclic organophosphoric esters is not particularly limited, and for example, those having an average particle diameter of 0.01 to 50 ⁇ m are usable. For homogeneously dispersing the particles, however, it is preferred to pulverize them into fine particles having an average particle diameter of 10 ⁇ m or below, particularly 3 ⁇ m or below.
- the amount of the basic polyvalent metal salts of cyclic organophosphoric esters is 0.01 to 5 parts by weight, preferably 0.03 to 3 parts by weight, for 100 parts by weight of the crystalline synthetic resin.
- the ratio of the alkali metal salt compound (a) to the basic polyvalent metal salt of cyclic organophosphoric ester (b) is not particularly limited, the effect of the present invention becomes remarkable when the amount of the component (a) is at least equivalent to that of the component (b).
- Examples of the crystalline synthetic resins in the present invention include ⁇ -olefinic polymers such as low-density polyethylene, linear low-density polyethylene, high-density polyethylene, polypropylene, polybutene-1, poly-3-methylbutene and ethylene/propylene block and random copolymers; thermoplastic linear polyesters such as polyethylene terephthalate, polybutylene terephthalate and polyhexamethylene terephthalate; polyphenylene sulfide; polycaprolactone; and linear polyamides such as polyhexamethyleneadipamide.
- ⁇ -olefinic polymers such as low-density polyethylene, linear low-density polyethylene, high-density polyethylene, polypropylene, polybutene-1, poly-3-methylbutene and ethylene/propylene block and random copolymers
- thermoplastic linear polyesters such as polyethylene terephthalate, polybutylene terephthalate and polyhexamethylene ter
- the present invention is extremely useful when a crystalline ⁇ -olefinic polymers, particularly polypropylene resins such as polypropylene, ethylene/ propylene copolymer and a mixture of such a propylene polymer with another ⁇ -olefinic polymer is used.
- polypropylene resins such as polypropylene, ethylene/ propylene copolymer and a mixture of such a propylene polymer with another ⁇ -olefinic polymer is used.
- the present invention is applicable irrespective of the limiting viscosity, isotactic pentad fraction, density, molecular weight distribution, melt flow rate and rigidity of such a polypropylene resin.
- the present invention is suitably applicable to also polypropylene resins described in Japanese Patent Laid-Open Nos. 37148/1988, 37152/1988, 90552/1988, 210152/1988, 213547/1988, 243150/1988, 243152/1988, 260943/1988, 260944/1988, 264650/1988, 178541/1989, 49047/1990, 102242/1990, 251548/1990, 279746/1990 and 195751/1991.
- the components can be added to the resin by any ordinary method such as a method which comprises dry-blending the crystalline synthetic resin powder or pellets with powdery additives, or a method which comprises preparing a master batch comprising the components in a high concentration and adding the master batch to the crystalline synthetic resin.
- the crystalline synthetic resin composition of the present invention can be used in the form of various moldings, fibers, biaxially oriented films and sheets formed by well-known molding methods such as extrusion molding, injection molding, vacuum molding, blow molding or crosslinking foaming molding.
- the crystalline synthetic resin composition of the present invention can be used as a material which is to be after-treated by various methods such as one to be sterilized by irradiation for use in medical treatment or as packaging material for foods, or one to be treated with a low-temperature plasma for improving the surface properties such as coatability after the molding.
- the resistance of the crystalline synthetic resin composition of the present invention to oxidation and light can be further improved, if necessary, by adding a phenolic antioxidant, an organophosphorus antioxidant such as an organophosphite or phosphonite, a thioether antioxidant; or a light stabilizer such as an infrared absorber or a hindered amine compound.
- a phenolic antioxidant and/or an organophosphorus antioxidant are examples of phenolic antioxidant, an organophosphorus antioxidant such as an organophosphite or phosphonite, a thioether antioxidant; or a light stabilizer such as an infrared absorber or a hindered amine compound.
- the phenolic antioxidants include 2,6-di-tert-butyl-p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, stearyl (3,5-di-tert-butyl-4-hydroxyphenyl)propionate, distearyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, thiodieyhylenebis[(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 4,4'-thiobis(6-tert-butyl-m-cresol), 2-octylthio4,6-di (3,5-di-tert-butyl-4-hydroxyphenoxy)-s-triazine, 2,2'-methylenebis(4-methyl-6-tert-butylphenol), bis[3,3-bis(4-hydroxy-3-tert-butylphenyl)butyric acid]/glycol ester, 4,4
- the amount of the above-described phenolic antioxidant used is preferably 0.001 to 5 parts by weight, still preferably 0.01 to 3 parts by weight, for 100 parts by weight of the synthetic resin.
- the organophosphorus antioxidants include trisnonylphenyl phosphite, tris(mono- and dinonylphenyl) phosphites, tris(2,4-di-tert-butylphenyl) phosphite, di(tridecyl) pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl) pentaerythritol diphosphite tetra(tridecyl)isopropylidenediphenol diphosphite, tetra(tridecyl) 4,4'-
- the amount of the above-described organophosphorus antioxidant is preferably 0.001 to 5 parts by weight, still preferably 0.01 to 3 parts by weight, for 100 parts by weight of the crystalline synthetic resin.
- the thioether antioxidants include dialkyl thiodipropionates such as dilauryl, dimyristyl, myristyl stearyl and distearyl thiodipropionates; and polyol ⁇ -alkylmercaptopropinates such as pentaerythritol tetra( ⁇ -dodecylmercaptopropionate).
- the ultraviolet abserbers include 2-hydroxybenzophenones such as 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone and 5,5'-methylenebis(2-hydroxy-4-methoxybenzophenone); 2-(2-hydroxyphenyl) benzotriazoles such as 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-3,5-di-tert-butylphenyl)5-chlorobenzotriazole, 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3,5-dicumylphenyl)benzotriazole, 2,2'-methylenebis(4-tert-octyl-6-benzotriazolyl)phenol, and polyethylene glycol ester of 2-(2-hydroxy
- the light stabilizers such as hindered amine compounds include hindered amines, e-g., 2,2,6,6-tetramethyl-4-piperidyl stearate, 1,2,2,6,6-pentamethyl-4-piperidyl stearate, 2,2,6,6-tetramethyl-4-piperidyl benzoate, bis(2, 2,6,6-tetramethyl-4-piperidyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, tetrakis (2,6,6-tetramethyl-4-piperidyl)butanetetracarboxylate, tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl) butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) di(tridecyl) 1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-
- the crystalline synthetic resin composition of the present invention any contain, if necessary, a nonionic, cationic or anionic antistatic agent; another nucleatin G agent such as aluminum p-tert-butylbenzoate, dibenzylidenesorbitol or bis(4-methylbenzylidene)sorbitol; hydrotalcite; an aliphatic carboxylic acid salt of an alkaline earth metal; as well as a pigment, dye, filler, foaming agent, flame retardant, lubricant, processing assistant, etc.
- a nonionic, cationic or anionic antistatic agent such as aluminum p-tert-butylbenzoate, dibenzylidenesorbitol or bis(4-methylbenzylidene)sorbitol
- hydrotalcite an aliphatic carboxylic acid salt of an alkaline earth metal
- a mixture of the following ⁇ recipe> was mixed on a mixer for 5 min and then extruded on an extruder at a temperature of 230° C. at a rotation rate of 20 rpm to form pellets.
- the pellets were molded into test pieces each having a thickness of 1 mm on an injection molding machine at 250° C. at a mold temperature of 60° C.
- the haze value (original) of the test pieces thus obtained was determined according to the method of ASTM D-1003-61.
- the haze value of the test piece was determined also after immersion in hot water at 80° C. for 36 h.
- Table 1 wherein the term "comparative compound” refers to the compound given below.
- a mixture of the following ⁇ recipe> was mixed on a mixer for 5 min and then extruded on an extruder at a temperature of 230° C. at a rotation rate of 20 rpm to form pellets.
- the pellets were molded into test pieces each having a thickness of 1 mm on an injection molding machine at 250° C. at a mold temperature of 60° C.
- the haze value of the test piece thus obtained was determined in the same manner as that of Example 1.
- Izod impact strength at 20° C. was also determined according to ASTM D-256 (kg.sup. ⁇ cm/cm 2 , hereinafter referred to merely as "impact strength") in Table 2. The results are given in Table 2.
- a mixture of the following ⁇ recipe> was mixed on a mixer for 5 min and then extruded on an extruder at a temperature of 240° C. at a rotation rate of 20 rpm to form pellets.
- the pellets were molded into test pieces each having a thickness of 1 mm on an injection molding machine at 250° C. at a mold temperature of 60° C.
- the haze value of the test piece thus obtained was determined in the same manner as that of Example 1.
- Test pieces having a thickness of 3.5 mm were prepared in the same manner as that described above, and irradiated with 5 Mrad ⁇ -rays using cobalt 60 as the ray source.
- the Izod impact strength at 23° C. of each of the test pieces heated at 100° C. for 10 days after the irradiation with the ⁇ -rays and the test pieces which had not been irradiated with the ⁇ -rays was determined according to JIS K 7110. The results are given in Table 3 below.
- pellets were melted at 280° C. for 10 min and then the temperature was lowered at a rate of 5° C./min to measure the crystallization temperature during temperature fall.
- the ratio (H/W) of the height H of the endothermic peak during the temperature fall to the width W at a height of H/2 was determined.
- the effect thereof is practically unsatisfactory and particularly the transparency improving effect thereof is insufficient, though the mechanical strengths and crystallization rate of the crystalline synthetic resin are improved to some extent.
- the improving effect is also insufficient when a combination of the alkaline earth metal carboxylate or alkali metal hydroxide with the basic polyvalent metal salt of cyclic organophosphoric ester or a combination of the alkali metal carboxylate with a metal salt of a cyclic organophosphoric ester other than the component (b) of the present invention is used.
- composition of the present invention containing the combination of the alkali metal salt compound with the basic polyvalent metal salt of cyclic organophosphoric ester exhibits further improved mechanical strengths and a remarkably improved transparency which has been insufficient in the prior art.
- the effect of the present invention is extremely specific.
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Abstract
Description
______________________________________ <Recipe> parts by weight ______________________________________ ethylene/propylene random copolymer 100 (ethylene content: 3 wt. %, MFR: 5.0 g/10 min) tetrakis[methylene 3-(3,5-di-tert- 0.1 butylphenylpropionate]methane tris(2,4-di-tert-butylphenyl) 0.1 phosphite sample compound (see Table 1) 0.1 lithium laurate 0.1 comparative compound ##STR4## ______________________________________
TABLE 1 ______________________________________ Haze after immersion in original hot water No. Sample compound % % ______________________________________ Comp. Ex. 1-1 none 32 35 1-2 sodium 2,2'-methylene- 17 28 bis(4,6-di-tert-butyl- phenyl) phosphate (comp. compound) 1-3 Compound No. 1 24 31 (calcium laurate used instead of lithium laurate) Ex. 1-1 compound No. 1 5 7 1-2 compound No. 2 8 10 1-3 compound No. 3 6 9 1-4 compound No. 4 5 8 1-5 compound No. 5 5 8 1-6 compound No. 6 6 8 ______________________________________
______________________________________ <Recipe> parts by weight ______________________________________ crystalline ethylene/propylene 100 random copolymer (ethylene content: 2.5 wt. %, MFR: 7.0 g/10 min) 2,6-di-tert-butyl-4-methylphenol 0.2 stearyl β-(3,5-di-tert-butyl- 0.1 4-hydroxyphenyl)propionate hydrotalcite (DHT-4A; a product of 0.05 Kyowa Chemical Industry Co., Ltd.) bacic polyvalent metal salt of cyclic 0.2 organophosphoric ester (compound No. 1) sample compound (see Table 2) see Table 2 ______________________________________
TABLE 2 ______________________________________ Haze Impact No. Sample Compound Amount % Strength ______________________________________ Comp. Ex. 2-1 none -- 27 13.2 2-2 calcium stearate 0.10 28 13.1 2-3 lithium stearate*.sup.1 0.10 19 13.4 2-4 lithium stearate*.sup.2 0.10 35 8.5 Ex. 2-1 sodium stearate 0.10 6 14.9 2-2 lithium stearate 0.02 9 14.2 2-3 lithium stearate 0.04 9 14.5 2-4 lithium stearate 0.06 6 15.3 2-5 lithium stearate 0.10 5 15.4 2-6 lithium stearate 0.20 5 15.4 2-7 lithium 12-hydroxy 0.10 5 15.3 stearate 2-8 lithium laurate 0.10 5 15.4 2-9 lithium naphthenate 0.10 6 15.3 2-10 lithium benzoate 0.10 7 14.8 2-11 lithium lactate 0.10 7 14.7 2-12 lithium β-dodecylmer- 0.10 5 15.0 captopropionate 2-13 lithium β-N-methyl-N- 0.10 6 14.8 lauroylaminopropionate 2-14 lithium acetylacetonate 0.10 6 15.0 2-15 lithium laurylaceto- 0.10 6 14.9 acetate ______________________________________ *.sup.1 The comparative compound was used in place of compound No. 1. *.sup.2 No compound No. 1 was added.
______________________________________ <Recipe> parts by weight ______________________________________ propylene homopolymer 100 (MFR: 6 g/10 min) bis(2,6-di-tert-butyl-4-methyl- 0.05 phenyl)pentaerythritol diphosphite 1,6,11-tris[2,4-bis(N-butyl-N- 0.1 (2,2,6,6-tetramethyl-4-piperidyl)- amino)-s-triazin-6-ylamino]undecane sample compound (see Table 3) 0.2 lithium stearate 0.15 ______________________________________
TABLE 3 ______________________________________ Izod impact strength before after γ-ray γ-ray irradn. Haze irradn. (heated for No. Sample Compound value (original) 10 days ______________________________________ Comp. Ex. 3-1 comparative 33 3.6 2.5 compound 3-2 compound No. 1 30 3.8 3.1 (lithium hydroxide used instead of lithium stearate) 3-3 compound No. 1 35 3.6 2.4 (calcium stearate used instead of lithium stearate Ex. 3-1 compound No. 1 23 4.7 4.4 3-2 compound No. 2 26 4.3 4.0 3-3 compound No. 3 24 4.5 4.2 3-4 compound No. 4 23 4.6 4.2 3-5 compound No. 5 23 4.6 4.3 3-6 compound No. 6 24 4.5 4.3 ______________________________________
TABLE 4 ______________________________________ Crystg. temp. during during Sample temp. rise temp. fall No. compound °C. °C. H/W ______________________________________ Comp. Ex. 4-1 none 138 191 7 4-2 comparative 123 204 13 compound Ex. 4-1 Compound No. 1 114 221 26 4-2 Compound No. 2 116 218 22 4-3 Compound No. 3 115 219 23 4-4 Compound No. 4 115 219 24 4-5 Compound No. 5 114 220 25 4-6 Compound No. 6 115 220 24 ______________________________________
Claims (8)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP03322153A JP3046428B2 (en) | 1991-12-05 | 1991-12-05 | Crystalline synthetic resin composition |
US08/026,479 US5342868A (en) | 1991-12-05 | 1993-03-04 | Crystalline synthetic resin composition |
DE69319578T DE69319578T2 (en) | 1991-12-05 | 1993-03-29 | Crystalline resin composition containing a Group III or IV metal salt with a cyclic phosphoric acid ester |
EP93105144A EP0622404B1 (en) | 1991-12-05 | 1993-03-29 | Crystalline synthetic resin composition containing a group III or IV metal salt of a cyclic organophosphoric ester |
ES93105144T ES2118847T3 (en) | 1991-12-05 | 1993-03-29 | COMPOSITION OF CRYSTALLINE SYNTHETIC RESIN CONTAINING A METAL SALT IN GROUP III OR IV OF A CYCLIC ORGANOPHOSPHORIC ESTER. |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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JP03322153A JP3046428B2 (en) | 1991-12-05 | 1991-12-05 | Crystalline synthetic resin composition |
US08/026,479 US5342868A (en) | 1991-12-05 | 1993-03-04 | Crystalline synthetic resin composition |
EP93105144A EP0622404B1 (en) | 1991-12-05 | 1993-03-29 | Crystalline synthetic resin composition containing a group III or IV metal salt of a cyclic organophosphoric ester |
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US5342868A true US5342868A (en) | 1994-08-30 |
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US08/026,479 Expired - Lifetime US5342868A (en) | 1991-12-05 | 1993-03-04 | Crystalline synthetic resin composition |
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EP (1) | EP0622404B1 (en) |
JP (1) | JP3046428B2 (en) |
DE (1) | DE69319578T2 (en) |
ES (1) | ES2118847T3 (en) |
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US5717013A (en) * | 1995-08-23 | 1998-02-10 | Tonen Chemical Corporation | Polypropylene resin composition |
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US5922793A (en) * | 1996-12-27 | 1999-07-13 | Minnesota Mining And Manufacturing Company | Modifying agents for polyolefins |
US5929146A (en) * | 1996-12-27 | 1999-07-27 | Minnesota Mining And Manufacturing Company | Modifying agents for polyolefins |
US5981636A (en) * | 1996-12-27 | 1999-11-09 | 3M Innovative Properties Company | Modifying agents for polyolefins |
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US6534574B1 (en) | 2001-03-24 | 2003-03-18 | Milliken & Company | Highly nucleated thermoplastic articles |
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US20030096723A1 (en) * | 2001-10-19 | 2003-05-22 | Ghee-Hong Jin | Protease obtained from Vibrio metschnikovii variants and detergent compositions comprising the above protease |
US20030127768A1 (en) * | 2001-12-21 | 2003-07-10 | Morin Brian G. | Method of producing low-shrink polypropylene tape fibers |
US20030134118A1 (en) * | 2001-12-21 | 2003-07-17 | Morin Brian G. | Low-shrink polypropylene tape fibers |
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Also Published As
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EP0622404B1 (en) | 1998-07-08 |
JP3046428B2 (en) | 2000-05-29 |
ES2118847T3 (en) | 1998-10-01 |
EP0622404A1 (en) | 1994-11-02 |
DE69319578T2 (en) | 1999-04-15 |
JPH05156078A (en) | 1993-06-22 |
DE69319578D1 (en) | 1998-08-13 |
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